Methyl 3-[4-(benzyloxy)phenyl]propanoate → 3-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl ester

HRID 459395Notes

Reaction equation

HRID 459395 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:21][CH2:22][CH3:23])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)C.COC(=O)C(OC)CC1C=CC=C(OCC2C=CC=CC=2)C=1.COC(=O)CCC1C=CC(OCC2C=CC=CC=2)=CC=1>>[CH3:1][O:3][C:4](=[O:24])[CH:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoateHCID 54423854Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoateHCID 588226203-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 219309623-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl esterYield 47.1%

Procedure

The title compound was prepared from 3-(4-benzyloxy-phenyl)-2-ethoxy-acrylic acid ethyl ester (Example 375, Step 2) (3.3 gr, 10.12 mmol) via the same procedure used for the preparation of 3-(3-benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 291, Step 3) to produce an oil that was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1) to produce two compounds: 3-(4-benzyloxy-phenyl)-propionic acid methyl ester (1.5 gr, Rf aprox. 0.65) and the desired compound (1.5 gr, Rf aprox. 0.2).

Workup

  1. customto produce an oil that
  2. customwas purified by chromatography (silica gel, hexanes/ethyl acetate 6:1)
  3. customto produce two compounds

Sources & evidence

ORD record
ord-cbb72b231ebd4783aca63fbfbd482710
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…